The Boston Celtics entered this offseason with a clear mission: escape the suffocating grip of the NBA’s second apron. Jayson Tatum’s devastating Achilles injury during the playoffs only intensified their resolve, pushing the front office to make bold moves to reshape the roster and gain financial breathing room. By trading away Jrue Holiday, Kristaps Porzingis, and Al Horford, and opting for restraint in free agency, the Celtics have carved out newfound flexibility. But one move stands out as both intriguing and telling: the acquisition of Anfernee Simons from the Portland Trail Blazers in the Holiday trade.
Simons, a dynamic scoring guard on an expiring $27 million contract, arrived in Boston as a talented but temporary piece of the puzzle. With the Celtics opting not to extend his deal before the season, the writing is on the wall: Simons’ time in green and white may be short-lived.
A Talented Misfit in Boston’s Backcourt
Almost immediately after the trade was finalized, Simons found himself at the center of trade rumors. The Celtics are reportedly open to flipping the 26-year-old guard before the season tips off in October, though they wouldn’t mind him suiting up for opening night if the right deal doesn’t materialize. On paper, Simons is a compelling addition. He’s a proven offensive weapon, averaging around 20 points, five assists, and shooting 38 percent from beyond the arc in recent seasons. With Tatum sidelined for most of the upcoming campaign, Boston desperately needs players to step up and fill the offensive void. Simons, with his scoring prowess and playmaking ability, could theoretically help shoulder that load alongside Jaylen Brown.
But there’s a catch—Simons’ skillset overlaps heavily with that of Payton Pritchard, the reigning Sixth Man of the Year. Pritchard is poised for a breakout season, taking on a significant on-ball role in Tatum’s absence. His career-best performance last year showcased his ability to spark the offense, and he’s cemented himself as a cornerstone of Boston’s guard rotation alongside Derrick White. The issue? Both Simons and Pritchard are defensive liabilities, making it nearly impossible for them to share the court effectively. Head coach Joe Mazzulla might toy with small-ball lineups featuring Simons, Pritchard, and White, but the defensive shortcomings of such a trio would likely outweigh any offensive upside. The fit, simply put, feels clunky.
A $27 Million Question Mark
Paying Simons $27 million to come off the bench behind Pritchard and White is a tough pill to swallow for a team meticulously managing its salary cap. His contract expires at the end of the season, so Boston could let him walk in free agency without long-term consequences. However, keeping him as a pricey reserve doesn’t align with the Celtics’ goal of optimizing their roster for both the present and the future. Trading Simons for a player who better complements the team’s needs—particularly in the frontcourt—makes far more sense.
Boston’s guard depth is already a strength, with Pritchard and White leading the charge. What the Celtics lack, however, is stability at center and forward after parting ways with Porzingis and Horford. A trade involving Simons could net a versatile big man or a defensive-minded wing, addressing critical roster gaps and creating a more balanced lineup around Brown and the returning Tatum.
Playoffs or Pivot? Boston’s Path Forward
The Eastern Conference is wide open this season, with no clear juggernaut dominating the landscape. For the Celtics, the path forward is uncertain. Do they push for a playoff spot, banking on Brown, Pritchard, and White to carry the load? Or do they take a step back, using Tatum’s absence as an opportunity to retool for a stronger future? Regardless of the direction, Simons feels like a square peg in a round hole. His offensive talents are undeniable, but his defensive limitations and redundancy with Pritchard make him a poor long-term fit.
The Celtics’ front office has shown a knack for making calculated, forward-thinking moves, and trading Simons before the deadline—or even before the season starts—seems like the logical next step. His days in Boston may be numbered, but his departure could pave the way for a roster better equipped to navigate the challenges of a Tatum-less season and beyond.
As the countdown to opening night continues, one thing is clear: Anfernee Simons’ destiny with the Celtics is set in stone, and it points to a future elsewhere. Boston’s championship aspirations, even in a transitional year, demand a roster that fits together seamlessly—and Simons, for all his talent, simply isn’t part of that vision.